Career Change: Overcome the Top 3 Challenges

By Upskill Coach, On May 07th 2019


It always seems impossible until it’s done.” – Nelson Mandela.

Bored in your current job? Unsatisfied and itching for something different? Have no idea on how to embark on a career change? Based on my own experiences, I will explain how you can achieve change, and find a career to fall in love with. It really is possible!

For context, let me give you some background history into my work experience. I was offered a shiny new job abroad while I was still in my final year of university. Unrelated to the course I had studied, the job came with a fat paycheck and plenty of perks strategically designed to keep me tethered to the post.

I enthusiastically jumped on board only to shortly after become aware that something was missing. I wasn’t satisfied. In fact, I was super bored and quickly realized that I could never reach my potential there. Although miserable, I did not know how to break the tedious cycle I now found myself in. One year at the company turned into four. I needed to get out but how?   

The good news is that I eventually managed to break free. It wasn’t an easy journey but with a little perseverance, I managed to reach the finish line. Sound interesting? Read on to learn how you can do the same.


1. Your biggest obstacle is you.

What you need to do is look at that obstacle thought, see that it can be turned into a strategy that then you can implement in terms of achieving your goal.” – Brooke Castillo, The Life Coach School. 

While working for that company, there were signs everywhere telling me that I needed to get out: I was embarrassed to talk about my work; I was ashamed about how my colleagues and I were being treated; I was frustrated that none of us ever did anything about our situations for fear of being fired; and I was terrified that I would reach retirement age without having enjoyed a fulfilling career propelled by work I could feel proud of.

I was completely uninspired by the meaningless work that I was doing. At the same time, I felt stuck. I knew I needed to make a career change but I had no idea where to start. My self-confidence had taken a hit and I couldn’t figure out what my options were.

In hindsight, my view of the working world was a little obscured. After all, this was my first full-time job and my knowledge of other industries was pretty limited. My lack of experience in the working world was a distinct disadvantage and I found it difficult to see the wood for the trees.

And of course other elements came into play: would I be able to earn the same salary elsewhere? Would I need to downsize my lifestyle? What would friends and family say? What if I quit and ended up on social welfare? These were all my own obstacles – created and curated by none other than myself. My lack of research and knowledge further fuelled by irrational fears held me back from a career change.

Does any of this resonate with you? Read on.

2. Practice what you preach.

You see, in life, lots of people know what to do, but few people actually do what they know. Knowing is not enough! You must take action.” – Tony Robbins.

I was an educator and a mentor: paid to teach, to solve problems, to coach individuals to realizing their potential and developing into human beings with a zest for life. Yet, I myself couldn’t figure out what I wanted to do. The irony of it still gets to me.

I used to come home from work and procrastinate rather than work on a plan of action. It was an easier alternative at the time. When I wasn’t procrastinating, I would be overthinking and analyzing my situation. A lot of thinking with very little doing.

In the hopes of having an awesome “lightbulb” moment, I completed a bunch of personality tests and online career guidance assessments. I read articles on business coaching and listened to motivational podcasts by life coaches. I trawled through social media checking out what connections were up to and researched to see how I could upskill to get into doing similar work.

You would think that if the answer to a career change lay in doing more analyzing, I’d have found a solution by this stage. And yet, I was no better off… still without immediate clarity or a sense of purpose.

3. You will not find a job just by looking for one.

In any moment of decision, the best thing you can do is the right thing. The worst thing you can do is nothing.” – Theodore Roosevelt.

Since going at it alone hadn’t paid off, I got in contact with recruitment agencies. I wanted a career change but I was unsure what path was right for me. Since I had no clear idea of what I wanted to do, the recruiters very quickly lost interest in helping me. As a potential jobseeker unsure of which career path to pursue, I had become a waste of time for them.

Nevertheless, I scrolled through every vacancy on all the job sites. I applied to everything and anything thinking that by doing this I might figure out what I wanted to do. In the process, I just made myself more miserable by repeatedly seeing that I didn’t have the relevant skills or experience for the jobs advertised. Rejection became a standard outcome and my sense of hopelessness increased. I knew I needed to upskill but how could I if I didn’t know what I wanted to do.

Unfortunately (and realistically), through no fault of your own, your lack of experience and skills will go against you when applying for jobs in a different field.

How I overcame the challenges, and you can too.

Here are solutions to those three challenges, but they may not be what you expect.

1. Don’t do it alone.

Your network is your net worth.”Porter Gale.

I was passive in my previous job. The thought of having to browse through new career options exhausted me. I wanted a change but I didn’t know how to go about it and the thought of risking my current job security only terrified me further.

I was comfortably uncomfortable.

Every now and then I would have a rush of energy to do something about my career. The flow was often interrupted by everyday activities and after a while, I would find myself back to square one and nothing had changed.

I decided I needed to let people in to help me figure things out and this prompted me to reach out to colleagues, family and friends. And all of a sudden, I began to make progress. I spoke to my colleagues; I spoke to trusted contacts who had also been through a similar situation. By making the effort to network with people from various industries my eyes were opened to a world of career possibilities.

And the outcome? New connections, new ideas, and most of all – accountability. This got the ball rolling.

Switching careers takes time and it definitely has plenty of ups and downs. But, it’s how you approach it (and who you approach) that makes all the difference. A problem shared is a problem halved. Talk to people – you never know where it may lead you. Think of connections as your personal support team.

2. Act it out, don’t figure it out.

Instead of thinking of the repercussions of action, you should also be asking yourself, ‘what are the costs of inaction?” – Tim Ferriss.

In my own journey of changing career, it took me four long years to admit (out loud and to those around me) that my job wasn’t the right fit for me and in an attempt to do the “mature” thing, I had failed to prioritize my own happiness  in my work and personal life.

I don’t want you to have to wait that long to make the choice to change career and to act on it. Don’t have analysis paralysis. It’s better to make a decision and fine tune your course along the way.

If you move from analyzing to acting, things will start to change for you!

Here are some things that I “acted” on:

I signed up to do a course in digital marketing. This was something I thought would be relevant to have on my CV as the whole world is turning digital. It’s a great course to have which in turn allowed me to open my mind to a whole world of opportunities that I didn’t think or know were available to me.

Another thing I did was job shadowing. I started with my brother who worked at two jobs – a music producer and the owner of an Irish gin business. It was nice to get a glimpse of worlds different from the one I had chosen. A glimpse of what could be. I did the same with the parent of a friend who worked as an interior designer for palaces in the Middle East. All equally fascinating careers, but not where I wanted to end up.

Nonetheless, I had made up my mind to take the plunge and seek out a new fulfilling job for myself. Job shadowing sparked ideas and excitement which helped me figure out aspects of a job that really interested me. I was now in a position to strike off career options and list job attributes that worked for me. Suddenly I felt empowered – like I was finally getting somewhere.

By the end of my contract, I had enough saved up to spend time testing ideas, travelling, being inspired and finding out what it was that I really wanted to do.

I began applying solely for digital marketing roles. I was enjoying my course and I knew this was something I definitely could do well. While on vacation, I had an interview with a startup and began working with them the following week. All the proactive steps I had taken to this point had led me to this job.

I am still on a journey of discovery and if there’s one thing I’ve learned along the way, it is that “taking action precedes clarity” – not the other way around.

3. Look for people, not jobs.

Communication – the human connection – is the key to personal and career success.” – Paul J Meyer.

The best place to start when you’ve made up your mind to go after a career change is networking. Connecting with people face-to-face allows you to present yourself in its entirety, not just the version of you as portrayed in an inanimate CV.

Personally, I consider myself an introvert – more comfortable meeting people or having video calls. And that’s what I did.

Don’t get me wrong. There were plenty of dead ends, but it led me to a role in a field I previously didn’t even know existed.

I was still in the middle of doing my professional diploma in digital marketing when I landed a job that I’m really enjoying. I wasn’t “qualified” for the role. However, I approached the role with lots of enthusiasm and a willingness to learn. It’s really difficult to convey that in a CV.

The job began as a digital marketing internship and for that, I am grateful, as lots of companies won’t take you on without experience. This allowed me to continue studying for my course while getting exposure to this new industry.

I wouldn’t have gotten this chance had I not made the decision to change. As the Buddhist proverb goes: “To know and not to do is not yet to know.”

It’s not easy to make a career change. Take it from someone who’s been down that road. But it is possible.

This is a life choice, not just a career choice. It’s about how you feel when you wake up every morning that affects your health and your relationships. Ultimately, it’s about the impact you make on the world through being alive in what you do.

So don’t just read this article and move on. Act on it. There’s no time like the now.

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